Films and television have provided us with countless images of men who teach. However, research shows that this is at odds with their relative absence from schools and in ‘real’ classrooms. This chapter explores why these numerous positive media-representations do not necessarily change the perception that teaching is generally seen as a career unsuitable or undesirable for men. Shared ideas of the characteristics that make teaching fulfilling and honourable live side by side in our collective perceptions as a result of media images of inspirational saviours and bumbling educators. Although these positive teacher images may contribute to men’s decisions to explore teaching as a career, many of them reconsider when harsh realities show the limits of these idealised portrayals. The strong connection between masculinity and the notion of the modern ‘career’ also has a role to play in men’s absence from a profession that somehow fails to be represented as a ‘real’ career for men. The necessity and demands of teacher preparation along with greater accountability and less autonomy combine to discourage many of those who consider education from completing programs and entering the field. Teacher educators and others must acknowledge that unrealistic media representations and existing obstacles and challenges do not necessarily have to result in fewer male teachers. An open discussion about what it really means to be a male teacher, with support and rewards, can counter the doubts and help them understand that teaching is a career for competent, caring men.